Why I Take Risks to Succeed, & How You Can Too


All my life, I've been different. As a child in elementary school, I climbed into the rafters rather than sitting at my desk. As a teenager, I loved getting lost in the city and trying to find my way home. I’ve always craved change, and challenges, and new perspectives.

That’s not always a good thing. Hunger for what’s new has led me down some self-destructive paths: a partial list might include an early pregnancy, partying too hard, running away from home, hitch-hiking, and dropping out of school.

My curiosity and search for novelty has also driven me to do things like writing and performing music, building companies, and travelling the world. And last week, it drove me out of a house I’ve called home for fourteen years, without a clear idea of when I might return.

I’m in LA. I’m here to grow the company I founded in new markets, but I’m also here to find what’s new. And there’s a lot of new. For the first time in my life, I feel like I’m surrounded infinite possibility. It scares the bejeezus out of me—and I may fail. I could lose everything. But I’m going to follow my dream anyway.

In the days since I announced my decision, a number of people have asked me whether I'm really doing this. Am I scared? How do I know if it's the right thing to do? There's a common theme to every question: "Why are you suddenly risking everything you have?”

The answer is simple. "Because I want to live in LA."


I’m terrified. I don't know if this is the right thing to do. But it is what I want to do. Perhaps more importantly, I’ve been preparing for it for years.

This is important to understand. This isn't a sudden decision, even though it might seem like it to many people who’ve known me for a long time. I just don’t talk about doing something much until I’m actually going to do it.

Maybe you have a dream. Maybe you’ve always wanted to live off the grid, or sail around the world, or take a year off and write a novel. My question to you is: “Why haven't you done it yet?"

I waited until this year because it’s the year my son graduates. He still needs me, but he will learn so much more, so much faster, if he has to provide for himself. And I’ll be in a better position to support him if I live in a big city with plenty of possibilities. He doesn't need a mom who cooks him dinner. As a talented 18 year old living in a small city, he needs opportunities.

What are you waiting for? Are you waiting for your kids to grow up? For your savings account to hit a certain point? For your aged relatives to die? (I know that's morbid, but it's often a valid reason to wait.)

We all have valid reasons to wait. But that doesn’t mean you should remain idle. You can plan and prepare, so that when the time comes, you’re ready to make the most of it. Here's what I did to prepare for the biggest change of my life:

  • Set a milestone. Mine was my son's graduation. Yours might be having enough money saved, or finishing school, or producing an album you can take on tour.
  • Meet and tell only the right people. I told people I met along the way who had made similar moves, and I learned their stories. I also told people I wanted to stay connected with, which is how I met my new roommates. Don't tell everyone else until you're ready to actually follow your dream. That’s because until you actually do something, it’s just a daydream. Daydreams can easily slide into the background of real life. You aren’t the daydream, you’re the change. If the daydream becomes more important than the plan itself, it’s easy to put off the change indefinitely.
  • Weave a safety net. Mine was my investment in my house, the sale of which will provide me (and my company) with a buffer while I figure out how to make the most of the new opportunities we'll find in LA.
  • Take care of your body. This is less obvious, but extremely important. You’re going to experience the craziest kinds of stress. It will be easier to deal with stress if you're healthy and you feel good about yourself. If you typically drink or do drugs to cope with stress, you’ll struggle a lot harder in a new place. I found a gym the day I landed. The next day I bought a ton of vegetables and made myself healthy meals for a week. I can’t afford to get sick here.
  • Lose the baggage. If you're tied to a relationship, a job, or another commitment that is preventing you from achieving your life's dream, extricate yourself. It will suck. You will hurt people. The alternative is resenting others because you feel you're missing out on your calling. Either way it's gonna suck—but there’s one option that could lead you towards happiness. The people you hurt also have that option. You can't make their decisions, but you get to make your own.

This article helped me. Maybe it will help you.

Just because you can’t make the change now doesn’t mean you can’t get ready. Start making the decisions you need to make to get you where you want to go, and you'll be surprised how easy it is to get there when the time comes. I started preparing over a decade ago, and now I’m ready.

The hard, exciting part is what comes next. :)